Although Wilson faced many challenges as President, he never neglected his duties as husband and father. His greatest source of strength had always been his family. Whether he was battling alumni at Princeton, taming Republicans in Congress, or arguing with Germans abroad, Wilson always found his home and his family to be his retreat, a place where he could escape from the battle lines and action. His home in the White House was no different. Wilson's wife, Ellen, was not only an intelligent, fun-loving companion, but an astute homemaker as well. Just as she had at Princeton and during Wilson's tenure as Governor of New Jersey, Mrs. Wilson made sure the White House was cheerful and happy. Although Mrs. Wilson did not enjoy large social gatherings in her home, the house was usually filled with music and laughter and dancing when the family of five was together. The family attended Sunday services regularly at the Central Presbyterian Church in Washington, D.C.

By the time Wilson become President, his three daughters Margaret, Jessie, and Eleanor had already grown to become young ladies and were soon attractive additions to Washington society. Mrs. Wilson noted the gentlemen that would frequently visit the family, and before Wilson had served two years as President, two of his daughters had been married in the White House. Jessie wed Francis B. Sayre on November 25, 1913, and Eleanor married Secretary of the Treasury William G. McAdoo in May of the following year.

Life for President Wilson, however, was not without hardship. In the summer of 1914–in the midst of Wilson's struggles in Mexico and Latin America and as World War I was just beginning to erupt in Europe–Mrs. Wilson became ill from tuberculosis. She died from kidney failure on August 6, 1914. Funeral services were held in Rome, Georgia, the town where the two had met decades earlier. The President was devastated and grieved deeply for months. To escape the pain, he immersed himself in his Presidential duties. He rose early each morning, worked straight through the day, and then continued working well into the night. He lost the will to live entirely, believing himself to be only a shell of a man after his wife's death.

In the end, it was family that kept Wilson alive. His eldest daughter, Margaret, who still lived in the White House with him, helped nurse him back to health. The grief eventually abated, and Wilson regained his outlook on life. By the summer of 1915, in fact, he had even fallen in love again. Wilson met Mrs. Edith Galt, the widow of a Washington jeweler, earlier that spring. Interestingly, their meeting that March was not their first: Mrs. Galt had once seen Wilson in a New Jersey parade during his brief term as Governor. At the time, she had noted his striking presence, but had made nothing of it. By 1915, however, that had completely changed. When he was not steering the nation clear of world war, fighting a miniature war in Mexico, or pushing his New Freedom reforms through Congress, Wilson spent his time writing love letters to Edith and sending her fresh flowers every day. The two married on the December 18, 1915. In finding new love, Wilson had also found new vigor.

With the 1916 election year fast approaching, Wilson began to evaluate his personal strength as President and the Democratic Party's strength as a whole. His conclusion: neither was excellent. By this time, many of Wilson's critics had begun attacking him as a cold and unfeeling man. True, Wilson conducted himself with a certain rigidity and self-righteousness that many others lacked, but he was by no means heartless. His enemies also attacked him for not having responded more harshly to the American deaths on the Lusitania. Additionally, the Democrats had lost much of their support from their more progressive members. Wilson believed that in order to be reelected, he had to accomplish three things: adhere to the public's demands for only moderate preparation for war with Germany, reunite the Democrats and the progressives, and finally, reaffirm his intentions to remain out of the Great War in Europe.

Wilson set out to accomplish each of these three tasks. He did prepare the United Sates for war, but only in moderation and without fully arming the country. He increased the size of the military and reserves. He also pushed for more progressive legislation to be passed: he succeeded in establishing an eight-hour working day for railroad workers, a national child labor law, and a worker's compensation program for federal employees. The Democratic campaign slogan during the 1916 election year was "He kept us out of war." Wilson's Republican opponent, former Supreme Court Justice Charles Evans Hughes, was not as successful as Wilson in accomplishing those goals that Wilson deemed so vital. Although Hughes and the Republicans agreed that the United States must remain out of the war, his policies were not progressive enough and by this time, neither were his party's.

Nevertheless, the election of 1916 was extremely close. Wilson completely lost the East and much of the Midwest to Hughes. As Election Day drew to an end, several newspapers set their presses to announce Hughes's victory. It is reported that Wilson himself fell asleep that night under the impression that he had lost. After all the votes had been counted, however, it was clear that Wilson had won. He had received roughly 600,000 more popular votes than had Hughes and twenty-three more votes in the Electoral College.

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